Supernatural: Where It Leads
by Jenessa Leigh Winchester
Summary: Set before the pilot, Sam Winchester had all he could take from his father John. After a huge fight one night Sam makes a life altering decision that could change the life of him and Dean forever. This does contain a bit of AU with Gilmore Girls stuff added.
1. Sam's Choice

**A/N: This story is about Sam's life before the pilot, What happen that night after the fight he had with John. Sam couldn't take it anymore and had to take some drastic action that could change his life and Dean's forever. Please note there are some Gilmore Girls stuff added into this and it's a bit of AU. :)**

 **Disclaimer: I do not own anything from Supernatural or Gilmore Girls. The only thing I own is my character Jenessa, Dean's daughter and Nicole because they are mine :)  
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Sam Winchester had always wanted to have a normal life, free from hunting and the supernatural since he was four-teen years old. There has been times over the years he and John had gotten into fights over having to move from town to town, living in rental houses and motels. Going back deep into Sam's life, he was only six months old when his mother, Mary was killed in a fire on November 2, 1983. Since then John had been trying to get revenge on the thing that killed her. His older brother Dean was mostly left to raise Sam when he was only five.

Then in Summer of 1996, Dean was only seventeen at the time when he met a girl from the school he was attending at the time. The two had been going out for a couple of weeks leading them to take it to the next level. Couple months later, Dean gets a call then later finds out that his girlfriend Nicole, was pregnant. They decided not to tell John about the pregnancy but Sam was told right away by Dean. Four months later, Nicole's parents found out and contacted John. He was livid..and there was a huge fight between Dean and him, He wasn't punished or anything it wasn't gonna do any good but they had to figure out how to raise his daughter.

Nicole decided to let Dean have the baby but does have visits from time to time. After the baby was born John finally learned to accept that Dean was a teenage father and helped him with the baby while trying to hunt. That was three years earlier. Dean nor John was ever ready for what was about to come next.

Sam did love his father even though the man cared more about hunting monsters out there..He wanted to protect the boys at any cost to. One night when Sam was only seventeen, He told Dean then his dad that he had been accepted to Standford with a full ride.. That didn't go well with John, causing a major blow out. This fight caused Sam to run out of the house and never return. It didn't help matters when John told him if he leaves he should stay gone.

A couple days after Sam had fled the house he was in a motel room watching TV and thinking about what had transpired between him and his dad. Nothing good ever came from hunting he thought. He had to do something..He stood up pacing back and fourth a bit in the room. He takes a deep breath pulling out his phone looking at the list, Finding Dean's he waited for a few minutes, then dialed his number. Dean answered the call after two rings. Sam was glad to hear his brothers voice..He was so close to him, He loved Dean with every being in his body.

Dean was happy to have heard Sam on the line he stood up from the kitchen table going into the other room to speak "Sammy, Hey buddy..I've been so worried about you, I know what happened the other night was bad gotta come home..he didn't mean it."

Sam sat on the side of the bed rubbing his eyes and sighs deeply "That's the thing Dean, He did mean it..I want to come home but I can't..I've been thinking..about things. I have to go away for awhile..

Dean felt alarm bells going off in his head he knew something wasn't right what did Sammy mean going away for a while he clears his throat to speak "Sammy? What are you talking about. I mean if you need some space thats fine but..

Sam sighs before speaking "No, Dean Thats not it..You might like what I'm about to do..but I'm telling you this because you're my brother and I love you. Just please don't tell dad okay" Sam could feel his head pounding all he wanted was some kind of freedom, Away from the hunting and the drama.

Dean paced back and fourth for a moment then spoke" Sammy, you're scaring me man, Listen I won't stay anything to dad but you gotta tell me what's going on, What are you about to do?" Dean was panicking inside and worried for his baby brother. He sighs going down the hall into the bedroom hoping that Sam doesn't do anything rash.

Sam was quiet for a moment then decided to speak "Dean, I'm not trying to scare you. It's just, I need to vanish for a bit from everything, this life and "Sam had paused for a moment before continuing" I promise I'll will give you the heads up on where I'm going, just please don't tell anyone even dad,

Dean rubs his eyes and pinches the bridge of his nose before speaking "Sammy, I don't like the sound of this. What about Standford? the collage you got accepted to? You know the entire reason why you had the fight with dad?

Sam rolls his eyes at the sarcastic tone Dean had and spoke "Yea I remember I was there during the fight, "He inhales a deep breath before speaking" Dean, don't worry about Standford. I can figure it out, Please Dean I need to do this.

Dean sighs even more before speaking "Sam, Alright, listen if I agree to this and I said "IF" There gonna be some conditions, I want you to call me and let me know where you are and if you're okay, I want updates on whatever or where-ever you're at. You can vanish from dad and the others but, I'm not gonna let my baby brother vanish from my life, Understood?

Sam chuckles hearing Dean laying down the rules he gets up getting a can of soda popping it open then takes a sip from it before speaking "Same ole Dean handing down rules, you know I thought you'd be tired of that by now. "He pauses for a moment before continuing" Alright, you got a deal Dean, I don't know where I'm gonna go yet but..I'll keep you updated.

Dean rolls his eyes at the rule comment and nods his head while listening to him on the phone "Good, I am glad to hear that. Sammy whatever you do out there remember you are still a teenager and this world is a crazy place, I'm not just talking about monsters either, There are people out there that are..You gotta watch your back okay?

Sam smiles some at Dean's concern and sighs "Yeah, I know and I will You don't have to worry about me Dean I know I'm seventeen now but I can handle things out there plus I still have protection if I need it.

Dean rolls his eyes hearing him and smirks a bit "Protection? Well that's good if you ever meet a girl you wouldn't want to get into the same trouble as I did when I was your age " Sam had to roll his eyes at that comment. Dean spoke up again after chuckling a bit to himself "I'm teasing you Sam, Be careful out there bro, Call me soon alright?

Sam inhales deeply and spoke "Yeah I will Dean you have my word on that." Sam said bye to Dean then sat down at the round table getting his laptop out, booting it up, While browsing the net he kept thinking back to the fight in his head. It was horrible he thought to himself plus he never thought he'd use the language he had done that night in all his life. Dean is right though, He was still a kid, planning a life on the run. He sat up in the seat after seeing a town that stood out to him, Looking it up he smiled to himself and realized where he was gonna go. "Stars Hollow" He muttered to himself.

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 **I hope you had enjoy reading the start, Next Chapter will talk about how he arrives in Stars Hollow, people that he met and whim finding his first love. Please note this story does contain Gilmore Girls in it though I placed it in Supernatural category because it's building it up before the pilot.. Sam's life before the series, I do hope you enjoy where this is going. Reviews and suggestions are welcomed :)**


	2. Stars Hollow: Fresh Start

Stars Hollow was a small town village located about 30 minutes from Hartford, CT. Sam spent most of his time researching that place before deciding it was somewhere he needed to go. That town looked fairly normal plus there had been no reports that any Supernatural has ever went on there. A week later Sam finally arrived in town after taking a taxi from Hartford. It was a sunny and beautiful day when he had arrived, Even the gazebo made it even more beautiful. He felt like the entire weight lifted off his shoulders. Sam walks down the street, coming up to Luke's Diner he decided to go inside for some coffee. Once sitting down at the bar counter a average tall man with a ball cap, looking rough around the edges came up to Sam to speak.

Luke was more of a moody type and fairly grumpy at times. He wasn't keen to newcomers like Sam. When he saw Sam he sensed the boy was trouble but didn't let on how he felt. He spoke up in a calm tone "Hello. What can I get you, young man?"

Sam looks up and sighs a bit after looking at the menu then spoke "Just some coffee is fine." Sam tone was quiet, He was rather shy himself being in a town what made it more uncomfortable was how some of the customers kept staring at him like he was an alien that arrived from the planet mars. pulling out his wallet, he didn't have much money left after taking a bus. Luke had poured Sam some coffee before speaking "So, you aren't from here are you?"

Sam didn't know how to answer that, He knew he was young and new to town with everyone staring, wondering who he was he sighs deeply shaking his head "I'm new here yes.. " Sam started to feel more out of place he decided to finish his coffee, when he did that he paid for it and left the Diner.

Sam inhales the clean air while walking across the street. He was lost and confused, Even questioning himself if this was a good idea after all. Suddenly a voice from behind him was heard. Sam turns around then noticed a woman much older than he was speaking to him. "Hi, Are you lost?"

Sam had to chuckle at that and nods" You could say that..I was just - " The woman nods her head in understanding then spoke up "Yeah I understand, I'm Barbra Forester I love just down the road there..are you new here..you seem fairly young."

Sam smiles a bit before speaking "Yeah, I..It's a long story..I really don't want to bother you with the details..Do you know if there's a motel or a place I could stay?" Barbra frowns a bit before speaking "A motel? No, but there is a Inn close by, Listen why don't you come over to my place, I could get you something to eat, you can rest..we could think of something to help you out." Sam didn't understand why this woman was being nice to him, He was a stranger in a strange town..Plus he wouldn't accept going into anyone's house like that but truth he was tired and worn out, Sam was reluctant and yet agreed.

A week had past since Sam arrived into Stars Hollow, The Forester family decided to let Sam stay with them after being found wandering the streets Although there were some changes when he took them up on the offer..plus he didn't think he was gonna be there long anyways.

Sam wasn't him anymore..He had told them he was Dean, taking his brothers name, he felt closer to Dean when he did that. He had met Clara, a young 11 year old whom would be seen as his sister. He was quite fond of young Clara, Helping her out when he could and helped around the house. The next big thing for Sam was school. He was told he needed to be in school, The teen was happy more so, elated to hear that..only he was seventeen at the time. He didn't seem to old so he let people think he was only sixteen.

School in stars Hollow had finally started that same week he was glad to be able to enroll into high school what he didn't know that his life was about to change too. One day Sam was standing outside of the school building on the stairs just thinking to himself when someone caught his attention. Two young girl one of them was was kind of Asian or Korean mixed walking with her friend, he was taken by the blue eye, brown hair girl, she looked like an angel. When they passed him talking about some hay ride in town his mouth fell open it was almost like his heart stopped beating in an instant. He needed to meet this girl for whatever reason he felt a sudden attraction to her.

After school that day Sam had gone home into his room, remembering that he hadn't spoken to Dean since before he gotten to Stars Hollow. He pulls out his cell, dialing his brothers number hoping he would answer and he did. "Dean?" Sam made sure his voice was low and the door closed he turned the radio up a bit so it could drown him out. "Hey Dean it's me."

Dean had heard Sammy on the other end of the line and the music playing rolling his eyes at the choice of music he spoke up "Sammy..Oh thank god you called I was sitting here getting worried it's been like two weeks since I've heard from you..are you okay?" He had alot of concern in his tone when speaking

Sam nods sitting on the bed speaking into the phone "Yeah, I'm great, never been better..Listen..so much has happened since I left..I'm alright Dean really.." Dean paced back and forth pitching the bridge of his nose all he wanted to was to grab his brother and bring him back home the truth that he couldn't. This had to be Sam's choice to come back home. "Sammy whats happening with you?" Sam could tell Dean was about to crack due to the tone of his voice and sighs some "Dean, nothing really..Look, I know it was hard that I left home but I needed to get out.."

Dean sighs some going to the fridge getting himself a bottle of beer sitting down before speaking "Yeah, I know, Dad was angry and scared when you told him about Standford it just.."Dean pauses for a moment he didn't want to beg the kid but couldn't live without him either." Where are you now?

Sam didn't say anything at first then spoke" I'm in Connecticut, A small town there about thirty minutes outside of Hartford..It's actually a nice place. Some of the people here are a little strange, not Supernatural strange though, that is a good thing. Uh Dean..has dad asked about me?"

Dean took a sip of his beer before speaking up" No, He didn't want to talk about it..he's not here now, He found himself a case, working on that..So you found a small town outside of Hartford? Hows that going?" Sam was a little disappointed that John didn't talk anymore about him, figures he thought.. He felt John was disappointed in him for wanted to do something with his life. Most dad would have been proud that their kid got a scholarship to collage in this case..His dad was different. "It's going great Dean..there is something I have to tell you though.."

Dean sighs deeply knowing Sam has done something hopefully nothing to bad he clears his throat before speaking "Alright, lets hear it then..I hope it wasn't anything crazy like getting married" Dean chuckled some at the teasing, Sam rolls his eyes shaking his head "No! I'm not that stupid plus I am seventeen, way to young for that. What I'm gonna tell you is not to bad I hope it isn't."

Sam explained how he was taken in by the Forester's and now living with them and their young daughter Clara. Also explained that he use his brother's name to hide his identity, also attending High School as a sixteen year old sophomore. Dean jaw dropped a bit hearing the explanation of all the years of knowing Sam he never thought he could pull that off, even taking his own name, Though he could understand why he did that.

It took a few minutes before Dean spoken up "Dude, you took my name? Oh I feel violated." He muttered that last part, taking a large drink from his bottle before continuing "Okay, so you faked your name and age, Attending school..I never thought you had the guts to pull that off, clever man."

Sam chuckles some before rolling his eyes and spoke" Dude, It's not like I'm pretending to be you..I don't have that James Dean type of image like you do" Sam laughs a bit at the teasing before continuing "Anyway there is something else, I saw someone recently, she was..Oh god you should have seen this girl she was the most beautiful you could ever seen!"

Dean blinked a couple of times before chuckling then smirks a bit "A girl, Aww that is so sweet and adorable..Little Sammy found himself a girl! My baby brother growing up! Let me guess you're gonna go up to her and hand her a dozen roses and recite her a lovely poem!? " Sam rolls his eyes again looking up and sighs listening to his brother teasing him big time "Very funny Dean..you are a riot I forgot your the king with the ladies. That's how you got yourself in trouble with one." Dean face wasn't amused by that then spoke "That wasn't funny Sammy! So I made a mistake it happens to alot of us"

"Only to the ones that don't use protection when they make love.." Sam said as he chuckled some, Dean rolls his eyes "Are you done? Good..now to be serious dude I think that is great you found someone you like just..be careful okay and Sam..don't worry your secret is safe with me." With that Sam said thank you and they both hung up. Now next step was to figure how to talk to the girl he had seen outside of the school.

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 **I hope you are enjoying the story so far! There is so much more coming soon. Next Chapter Sam meets Rory for the first time. Reviews and Suggestions are welcomed :)**


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